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Volumn , Issue 16, 2007, Pages 2509-2512

A novel and efficient synthesis of 2-aryl-2H-indazoles via SnCl 2-mediated cyclization of 2-nitrobenzylamines

(8) Shi, Da Qing a,b Dou, Guo Lan b Ni, Sai Nan b Shi, Jing Wen b Li, Xiao Yue b Wang, Xiang Shan b Wu, Hui b Ji, Shun Jun a

a SOOCHOW UNIVERSITY (China)

b JIANGSU NORMAL UNIVERSITY (China)

Author keywords

2 Aryl 2H indazole; 2 nitrobenzylamine; SnCl2

Indexed keywords

2 NITROBENZYLAMINE DERIVATIVE; 2H INDAZOLE DERIVATIVE; BENZYLAMINE DERIVATIVE; INDAZOLE DERIVATIVE; TIN CHLORIDE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL BOND; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; SYNTHESIS; X RAY DIFFRACTION;

EID: 35348976208 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2007-986665 Document Type: Article

Times cited : (40)

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29
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- 2O (6 mmol) in 95% EtOH (20 mL) was allowed to stir at 40°C for 2 h
- 2O (6 mmol) in 95% EtOH (20 mL) was allowed to stir at 40°C for 2 h. The reaction mixture was quenched with 3% HCl (100 mL), filtrated, the crude product was purified by crystallization from 95% EtOH to give the pure products 2.
- The reaction mixture was quenched with 3% HCl (100 mL), filtrated, the crude product was purified by crystallization from 95% EtOH to give the pure products , vol.2
- General¹

30
- 35349028552
- Representative Spectral Data for 2b 1H NMR (400 MHz, DMSO-d6, δ, 9.12 (s, 1 H, H-3, 8.10 (d, 2 H, J, 8.0 Hz, ArH, 7.78 (d, 2 H, J, 8.4 Hz, ArH, 7.72 (d, 2 H, J, 8.4 Hz, ArH, 7.46 (t, 1 H, J, 7.2 Hz, ArH, 7.32 (t, 1 H, J, 8.0 Hz, ArH, 7.11 (t, 1 H, J, 7.6 Hz, ArH) ppm. 13C NMR (100 MHz, DMSO-d6, δ, 149.12, 140.12, 129.86, 128.02, 126.96, 122.64, 122.28, 121.74, 121.11, 120.42, 117.65 ppm. IR (KBr, ν, 3131, 3066, 1626, 1593, 1518, 1494, 1464, 1407, 1378, 1349, 1314, 1250, 1231, 1201, 1143, 1129, 1073, 1044, 950, 907, 820, 780, 754, 685 cm-1. MS: m/z, 194 100, M, Anal. Calcd for C13H 10N2: C, 80.39; H, 5.19; N, 14.42. Found: C, 80.55; H, 5.29; N, 14.26
- 2: C, 80.39; H, 5.19; N, 14.42. Found: C, 80.55; H, 5.29; N, 14.26.

31
- 35348931268
- Crystallographic data for the structure of 2i has been deposited at the Cambridge Crystallographic Data Centre under the deposit number CCDC-655981. Copies of available material can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: +44 (1223)336033; e-mail: deposit@ccdc.cam.ac.uk, Crystal data for 2i: C14H10Cl2N2; M, 277.14, colorless block crystals, 0.43 x 0.40 x 0.32 mm, monoclinic, space group P21/c, a, 14.234(3) Å, b, 14.438(3) Å, c, 6.0511(15) Å, α, 90°, β, 92.338(7)°, γ, 90°, V, 1242.5(5) Å3, Z, 4, Dc, 1.481 g cm-1, F(000, 568, μ (Mo Kα, 0.503 mm-1. Intensity data were collected on a diffractometer with graphite monochromated Mo Kα radiation (λ, 0.71073 Å) using ω scan mode wi
- -1. Intensity data were collected on a diffractometer with graphite monochromated Mo Kα radiation (λ = 0.71073 Å) using ω scan mode with 1.43° < θ < 25.00°; 2183 unique reflections were measured and 1532 reflections with I > 2σ(I) were used in the refinement. The structures were solved by direct methods and expanded using Fourier techniques. The final cycle of full-matrix least squares technique to R = 0.0460 and wR = 0.1283.

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